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3-(Methylthio)propanoic acid → 4-tert-butyl-N-{4-chloro-5-fluoro-2-[N'-(3-methylsulfanyl-propionyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide

HRID 2238308
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HRID 2238308 반응식
[CH3:1][S:2][CH2:3][CH2:4][C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[C:14]([C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:33]=[C:32]([F:34])[C:31]([Cl:35])=[CH:30][C:29]=2[C:36]([NH:38][NH2:39])=[O:37])(=[O:26])=[O:25])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[C:14]([C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:33]=[C:32]([F:34])[C:31]([Cl:35])=[CH:30][C:29]=2[C:36]([NH:38][NH:39][C:5](=[O:7])[CH2:4][CH2:3][S:2][CH3:1])=[O:37])(=[O:25])=[O:26])=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]
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참가 물질

7

반응물 4

HCID 5633-(Methylthio)propanoic acidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 593029664-tert-butyl-N-(4-chloro-5-fluoro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide

생성물 1

HCID 593030414-tert-butyl-N-{4-chloro-5-fluoro-2-[N'-(3-methylsulfanyl-propionyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 3-methylsulfanyl-propionic acid (120 mg, 1.0 mmol) under an inert atmosphere in 6 mL of anhydrous DCM and DMF (200 μL) was added oxalyl chloride (89 μL, 1.0 mmol). The resultant solution was stirred at room temperature overnight and then added to a solution of 4-tert-butyl-N-(4-chloro-5-fluoro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide (400 mg, 1.0 mmol) and Et3N (0.35 mL, 2.5 mmol) at 0° C. The resultant solution was stirred at room temperature for 4 hours and the solvent was removed in vacuo. The residue was purified via automated silica gel chromatography to afford 4-tert-butyl-N-{4-chloro-5-fluoro-2-[N′-(3-methylsulfanyl-propionyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide as an oil: MS (ES) M+H expected 502.1, found 502.0.

후처리

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified

출처 및 근거

ORD 기록
ord-0bf3042bcf8e4332bc983cdcf5ebe102
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07718683B2

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